Showing metabocard for DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007257)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:43 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007257
Secondary Accession Numbers
  • BMDB07257
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2], also known as dg(18:2(9z,12z)/20:4(5z,8z,11z,14z)/0:0)[iso2] or DAG(18:2/20:4), belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s. These are dg(18:2(9z,12z)/20:4(5z,8z,11z,14z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Linoleoyl-2-arachidonoyl-sn-glycerolHMDB
DAG(18:2/20:4)HMDB
DAG(18:2N6/20:4N6)HMDB
DAG(18:2W6/20:4W6)HMDB
DAG(38:6)HMDB
DG(18:2/20:4)HMDB
DG(18:2N6/20:4N6)HMDB
DG(18:2W6/20:4W6)HMDB
DG(38:6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/20:4)HMDB
Diacylglycerol(18:2n6/20:4n6)HMDB
Diacylglycerol(18:2W6/20:4W6)HMDB
Diacylglycerol(38:6)HMDB
DiglycerideHMDB
1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolHMDB
DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C41H68O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,28,30,39,42H,3-10,15-16,20,23,25-27,29,31-38H2,1-2H3/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t39-/m0/s1
InChI KeyKRECEGQUDDMNAQ-MYBRWWDOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.23ALOGPS
logP12.5ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity202 m³·mol⁻¹ChemAxon
Polarizability79.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06s9-1194240000-7c18470313c08977ab1fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-1098005000-584b5938061287105a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1094121000-c4daf1d713525792f9bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1091130000-5a535a764678e95074b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gy9-0095003000-82bd99cbee6f5625d83eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1093000000-91ce5a327d3d1d454ed3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m2i-3092000000-c8687db4622a17e7dc19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-0697d21e1d6f73bcdbfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009004000-7ffbea8b11eed7c08883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009004000-777bb2457771df18712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p6-5187069000-a3e3fa69c87bbd5caf24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-3494000000-e681d813944d4b80ad24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1397000000-4543e54cbfc138baa432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1047009000-4e9e26e4a9b47e2de467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-5095001000-168a88a58caf2109a44dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0m29-5093000000-f4f707c38c2060cebd94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-ce78dc522fa40e0084e6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007257
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024450
KNApSAcK IDNot Available
Chemspider ID7822746
KEGG Compound IDC00165
BioCyc IDDIACYLGLYCEROL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543796
PDB IDNot Available
ChEBI ID89203
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))details
Enzyme Details
2. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails